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    • 专利摘要:
    The present invention contemplates a capture solution of carbon monoxide (co) comprising an ionic liquid, formed by a cation and an anion and a capture compound, where the anion of the ionic liquid (a) is not an element belonging to the group of the halogens (group 17) and where the capture compound (b) is a transition metal salt selected from those which can form reversible complexes with the co. It also contemplates a method for capturing and separating carbon monoxide (co) gas from a gas stream, comprising i) contacting the gaseous stream containing co with the capture solution of the invention, which eliminates the co of said current, ii) the selective and reversible reaction between the co and the transition metal salt, and iii) the regeneration of the capture solution and the recovery of the co contained therein. (Machine-translation by Google Translate, not legally binding)
    公开号:ES2612200A1
    申请号:ES201601107
    申请日:2016-12-23
    公开日:2017-05-12
    发明作者:Gabriel ZARCA LAGO；Ana María URTIAGA MENDÍA；Inmaculada Ortiz Uribe
    申请人:Universidad de Cantabria；
    IPC主号:
    专利说明:

     DESCRIPTION Method for the separation and purification of carbon monoxide from gas mixtures using ionic liquids 5 Object of the invention The present invention has its field of application within the chemical technology sector, in particular in the methods of gas separation. In particular, it refers to a solution for the absorption of carbon monoxide (CO) comprising an ionic liquid and a capture compound and a method based on the use of said solution for the selective separation of CO from a gas mixture which It contains CO, as well as for the regeneration of the capture solution and the recovery of the CO contained in it. BACKGROUND OF THE INVENTION Carbon monoxide (CO) is a gas of great industrial relevance, either pure or part of a mixture - known as synthesis gas - together with hydrogen (H2), for large-scale production of a wide range of basic chemicals including alcohols, aldehydes, carboxylic acids and pesticides, among many others. However, it is known that all processes of obtaining carbon monoxide, mainly processes of reforming and partial oxidation of hydrocarbons, as well as coal gasification, give rise to a mixture of gases that in addition to CO contains mainly H2 and CH4 , as well as significant amounts of C02 and N2 and other reduced sulfur and nitrogen compounds and volatile organic compounds in smaller quantities. In addition, carbon monoxide is obtained as a byproduct in various industrial processes, such as the manufacture of steel, carbon black, phosphorus, as well as in refineries 25 and petrochemical plants. The cost of the separation of CO, or of adjusting the CO / H2 ratio of the synthesis gas, contributes significantly to the cost of obtaining chemicals that use CO as raw material. Thus, once the main acid impurities have been eliminated, there are various methods to purify the CO depending on the characteristics of the feed and the final specifications required (NN Dutta and GS Pati !, Develapments ín CO separated, Gas Sep. Puríf , 1995, 9, 277-283). Among the most widely used methods for this purpose are cryogenic distillation processes, such as partial condensation at low temperatures (US 4478621 A; US 6173585 81 and US 6070430 A) or washing with liquid methane (US 6073461 35 A), as well as reactive absorption processes (US 2900347 AY G8 1318790 A). Other processes based on adsorption technologies in solid materials (US 4696682 A; EP 0367618 81) are only suitable for small and medium-scale applications, and therefore their use for the purification of CO is not very widespread, limiting their commercial use mostly to the purification of H2. 40 It is known that cryogenic distillation processes, in addition to being very energy intensive, due to the low temperatures (up to 80 K) and high pressures (up to 4 MPa) that need to be achieved to liquefy the CO, are less efficient the higher is the nitrogen content in the initial gas mixture, since the boiling points of CO and N2They are very close. In addition, these processes must first remove the CO2 contained in the gas mixture to avoid problems arising from freezing in the system under the aforementioned operating conditions. For their part, reactive absorption processes are capable of producing pure CO from a mixture of gases, including N2 enriched streams, by using absorbent liquids containing dissolved transition metals capable of forming reversible complexes with CO under more moderate pressure and temperature conditions, usually with temperatures between 308 and 318 KY pressures between 0.7 and 3 MPa. The most widespread process of reactive absorption of CO, which is currently marketed under the name of COPuréM, which replaces the COSORB® and COSORB II® processes, was invented by Esso Research and Engineering Company (US 3651159 A) and subsequently developed by Tenneco Chemicals (US 3767725 A). These processes employ a bimetallic salt of copper, mainly copper tetrachloroaluminate (l) (CuAICI4), dissolved in aromatic organic compounds, such as benzene and toluene (T. Sato et al., Chemical reaction of carbon monoxide with copper (l ) -tetrachloroaluminate (III) -aromatic hydrocarbon solutions -equilibrium and kinetics-, J. Chem. Eng. Jpn., 1988, 21, 192-198; Koschel et al., Absorption of CO, H2 and CH4 in toluene and copper ( l) tetrachloroaluminate-toluene solutions at elevated pressures, Energ. Fuels, 1991, 5, 729-733; Hoogendoorn et al., The absorption of carbon monoxide in COSORB solutions: 20 absorption rate and capacity, Chem. Eng. J., 1995 , 59, 243-252). Accordingly, these processes use chemicals that are classified as toxic and flammable according to Regulation (EC) No. 1272/2008 of the European Parliament and of the Council, of December 16, 2008, on classification, labeling and packaging of substances and mixtures . In addition, the use of volatile compounds, such as those mentioned above, contributes to increasing the energy requirements of the separation, since a part thereof evaporates as the temperature increases during the recovery stage of the absorbed gas and regeneration of the solution Capture Likewise, the use of solutions containing chloride anion can contribute significantly to generate corrosion problems in the equipment used. 30 Ionic liquids are liquids that are composed solely of anions and cations. The term ionic liquid usually refers to salts whose melting point is below 373 K. From the point of view of process safety and its environmental impact, ionic liquids offer numerous advantages over volatile solvents commonly used. in chemical processes since, in general, they are non-volatile substances - their vapor pressure is difficult to detect experimentally - non-flammable, they are in a liquid state in a wide range of temperatures and have a high thermal and chemical stability. Likewise, it is worth mentioning, as one of its main characteristics, the possibility of modifying the composition of the ionic liquid, for example by combining different cations and anions or incorporating hoisted functional groups, to adapt its physicochemical properties to those desirable to carry out a process determined. The use of ionic liquids as alternative solvents in physical and / or chemical absorption processes for gas separation has been widely explored, especially for the capture of acid gases such as CO2, S02 and H2S (US 2011014100 A 1; US 2005129598 A 1 ). 45 The physical solubility of light gases such as H2, N2, O2, CO, CH4 and other gaseous hydrocarbons has also been investigated (Lei et al., Gas solubility in ionic liquids, Chem Rev., 2014, 114, 1289-1326 ) although, the low physical solubility of light gases inIonic liquids hinders the development of efficient separation processes that operate in low pressure conditions. For its part, US 6623659 82 and US 2003125599 A1 describe compositions and methods for separating olefins from non-olefins and di-olefins from mono-5 olefins, respectively, by using capture solutions comprising an ionic liquid and a salt of a transition metal, preferably silver tetrafluoroborate or copper (I) chloride, which reacts selectively and reversibly with olefins and di-olefins forming a complex. The prior art concerning the use of ionic liquids for the reactive separation of 10 CO includes the documents David et al. "On the improved absorption of carbon monoxide in the ionic liquid 1-hexyl-3-methy / imidazolium chlorocuprate", Sep. Purif Technol., 2012, 97, 65-72 and Zarca et al. "Kinetics of the carbon monoxide reactive uptake by an imidazolium chlorocuprate (1) ionic liquid", Chem. Eng. J., 2014, 252, 298-304, which refer to a CO capture solution comprised of an ionic liquid and a copper salt (l). Specifically, they refer to the ionic liquid 1-hexyl-3-methylimidazolium chloride ([C6mim] [CI)) and the copper chloride salt (l) (CuCI). However, the development of new CO separation processes based on said capture solution is severely hampered. This is mainly due to the fact that ionic liquids containing anions belonging to the halogen group (group 17), in this case the chloride anion, 20 have extremely high viscosities, for example the viscosity of [C6mim] [CI] is 18.1 Pa sa 298 K. The consequences of using such high viscosity compounds are the extremely high investment and operating costs due to hydrodynamic problems and the serious limitations of the processes of matter and energy transfer. Also, although decreasing the carbon number of the cation alkyl chain usually results in less viscous ionic liquids, it is also true that this results in an increase in the melting point of these compounds which, in the case of ionic liquids with anions of the halogen group, they become ionic solids with low melting points and, consequently, are not in a liquid state at room temperature. For example, the melting points of ionic liquids 30 [C4mim] [CI] and [C2mim] [CI] are 341 and 360 K, respectively. Additionally, these ionic liquids whose anions are elements belonging to the halogen group can present problems of corrosion of materials with the consequent risks of failure and decrease of the useful life of the process equipment used (Uerdingen et al., Corrosion behavior of ionic liquids, Green Chem., 2005, 7, 321-325; Tseng et al., Corrosion behaviors 35 of materials in aluminum chloride-1-ethyl-3-methylimidazolium chloride ionic liquid, Elecfrochem. Commu.17, 12, 2010, 1091-1094 ). For these reasons, the development of carbon monoxide absorption processes in the solutions of ionic liquids with dissolved salts available or disclosed so far in the prior art does not seem feasible. Description of the figures Figure 1.-Absorption capacities of pure CO (293.15 K) of capture solutions based on the ionic liquid [C2mim] [SCN] and the copper salt (l) CuSCN. Figure 2.- Pure CO absorption capacity of capture solution number 5 of example 1 in the temperature range 273.15-303.15 K.Figure 3.- Reuse capacity of the CO capture solution. Absorption experiments of pure CO performed in a single capture solution (solution number 1 of example 1) in the temperature range of 273.15-303.15 K. The filled symbols show repeated experiments under the same temperature conditions as the 5 tests represented by the respective hollow symbols. Description of the invention Based on the needs of the state of the art in relation to the processes of carbon monoxide absorption, the inventors have developed a new composition that allows to overcome the problems derived from the use of ionic liquids as solvents. alternatives in these processes. Thus, the present invention relates to compositions and methods for separating carbon monoxide (CO) from its mixtures with other light gases such as H2, N2 or CH4. The compositions include solutions of transition metal salts, which can form complexes of the metal cation with CO, in ionic liquids. The methods involve contacting a mixture of CO-containing gases with a solution of a metal salt that complexes with the CO in an ionic liquid and, subsequently, the recovery of the absorbed CO and the regeneration of the capture solution. Gas mixtures containing CO can come from various sources such as 20 processes of reforming and partial oxidation of hydrocarbons, gasification of coal or gas streams obtained as a byproduct in other industrial processes, and in addition to CO they can contain other gases, mainly hydrogen, methane, nitrogen and carbon dioxide. The sulfur and nitrogen compounds present as impurities in said streams are preferably removed by techniques known in the state of the art. In a main aspect, the present invention relates to a CO capture solution (hereinafter composition of the invention) comprising: a) an ionic liquid, formed by a cation and an anion that does not belong to the group of halogens (group 17) and 30 b) a capture compound, which is a transition metal salt selected from those that can form reversible complexes with CO. In the present invention, "ionic liquid" means a fluid consisting of cations and anions characterized by having a melting point of less than 373 K, although those with a melting point of less than 298 K, commonly known as "liquids, are preferred." ionic at room temperature. " Examples of common cations are formed by cationized nitrogen or phosphorus atoms attached to several alkyl chains, which may be of equal or different number of carbon atoms, or which are part of aromatic and non-aromatic heterocyclic rings, which may also be substituted by one or several alkyl chains 40 with equal or different number of carbon atoms. Said alkyl chains are mainly formed by carbon and hydrogen atoms, although they may optionally be substituted, and may be linear or branched, cyclic or acyclic, with or without saturated bonds.In preferred embodiments of the composition of the invention, the alkyl chains have between 1 and 6 carbon atoms, since longer chains produce very viscous fluids. In the composition of the present invention, the ionic liquid anion is an element other than a halogen (ie, it does not belong to group 17 of the periodic table) and, preferably, is selected from the group of polyatomic species with load delocalization such as: thiocyanate, bis (trifluoroalkylsulfonyl) -imide, trifluoroalkylsulfonate, alkylsulfate, acetate, trifluoroacetate, etc. More preferably it is selected from thiocyanate, trifluoroalkylsulfonate, acetate and trifluoroaceto, and even more preferably, the anion of the ionic liquid is thiocyanate. Preferably, the ionic liquid has low viscosity, those ionic liquids with viscosities at room temperature below 0.1 Pa s being of special interest for this invention. Therefore, in preferred embodiments of the solution of the present invention, the anion employed is thiocyanate [SCNr. The use of thiocyanate anion makes it possible to use a cation with an alkyl chain of only two carbons, which is an advantage in terms of viscosity reduction. In particular embodiments of the composition of the invention, the ionic liquid cation is selected from the group of imidazoliums, preferably from the group consisting of 1-ethyl-3-methylimidazolium, 1-butyl-3-methylimidazolium and 1-hexyl-3-methylimidazolium . The choice of one cation 20 or another will affect the physical properties of the capture solution, so that the criteria of lowest possible viscosity, lowest melting point, non corrosivity, etc. would apply. The metal salts used as the capture compound are selected from among the transition metals known to form chemical complexes with CO, such as copper (l), silver (I), nickel (II), cobalt (II), iron ( II), manganese (II), magnesium (II), zinc (II), etc. The concentration of the dissolved metal salt in the ionic liquid typically varies between 0 and 30 mol%, but the concentration may be higher depending on the solubility of the salt in the ionic liquid. In preferred embodiments, the metal salt is selected from among copper (l) thiocyanate (CuSCN), copper (l) acetate (CuC02CH3), copper trifluoromethanesulfonate (l) (CuCF3S03) and copper (l) trifluoroacetate (CuC02CF3) . In even more preferred embodiments, the metal salt is thiOn ato of copper (l) (CuSCN). In a preferred embodiment of the invention, the composition is formed by dissolving the metal salt of copper thiocyanate (1) (CuSCN) in the ionic liquid 1-ethyl-3-methylimidazolium thiocyanate [C2mim] [SCN]. The authors of the present invention have experimentally determined that the ionic liquids used in the dissolution of the present invention have a great tendency to be in a subcooled state, that is, they are kept in a liquid state below their theoretical melting point. In the case of [C2mim] [SCN] the results show that it is in a liquid state even at 193 K, a temperature that is sufficiently low compared to the usual one in these chemical absorption processes. In another main aspect of the invention, a method is contemplated for the capture and separation of CO from a gas stream (hereinafter method of the invention) comprising the following steps: i) bringing the current into contact gas containing CO with a capture solution, as defined in the present invention, that5 removes the CO from said stream, ii) the selective and reversible reaction between the CO and the transition metal salt; and iii) the regeneration of the capture solution and the recovery of the CO contained therein. In particular embodiments of the method of the invention, the gas stream contains CO together with other gases, mainly H2, C02, CH4 and N2. Methods for separating CO from other light gases involve preparing a solution of a salt of a transition metal that complexes with the CO in an ionic liquid. The gas mixture containing CO is contacted with the capture solution of the invention in a combination of pressure and temperature conditions that favor that a part of the CO present in the gas mixture is absorbed into the capture solution due to the formation of a complex between CO and the transition metal. 15 The conditions for the development of the method (temperature, pressure, concentrations, etc.) must be subject in each case to a technical-economic analysis, routine for a person skilled in the art, for the optimization of these variables in the process. However, in preferred embodiments of the method of the invention, step i) is carried out by increasing the system pressure until reaching a final pressure between 20 6 and 25 bar and cooling the capture solution until reaching a final temperature between 273 and 303 K. The CO absorbed in the capture solution can be subsequently recovered by the appropriate combination of pressure and temperature conditions to reverse the complexation reaction between the CO and the transition metal. Thus, step iii) of the method of the present invention consists in subjecting the capture solution to desorption conditions to obtain a stream containing the recovered CO and a stream containing the regenerated capture solution and being able to be again used In particular embodiments, this step is carried out by heating the capture solution to a final temperature of between 333 and 473 K and reducing the pressure of the system until reaching a final pressure between 0.1 and 1 bar, in one or several stages. The advantages derived from the dissolution of the present invention, as well as the method for the absorption of CO based on its use, are: the high capacity of absorption of CO and the high selectivity against other light gases that are slightly soluble in ionic liquids such as H2, N2, CH4, etc., the ability to recover pure CO from its mixtures with other light gases such as H2, N2, CH4, etc., the high dissolution capacity of transition metal salts without adding ligands or of using bimetallic salts such as 40 CuAICI4, the low energy requirements for the regeneration of the ionic liquid, the high thermal and chemical stability of the capture solution and wide range of temperatures in the liquid state,5 10 the less or no corrosion of materials compared to the solutions containing anions of the halogen group, one of the most important advantages of the method of this invention is that the loss of the ionic liquid is very small or zero since the pressure vapor of the capture solution is extremely small, the possibility of completely regenerating the CO absorption capacity of the capture solution for reuse, a lower risk of operation and less toxicity than conventional solvents, such as toluene, since Ionic liquids are generally non-flammable compounds that have very low or practically zero volatility. EXAMPLES Example 1. Preparation of CO capture solutions. In this example, the compatibility and solubility of a copper salt (1) was analyzed, which is capable of forming species complexed with CO in a low viscosity ionic liquid. The ionic liquid and metal salt selected in this example were 1-ethyl-3-methylimidazolium thiocyanate, [C2mim] [SCN], whose viscosity at 298 K is 0.02 Pa s, and the copper salt (l) with the same anion, CuSCN. Both products were purchased from commercial suppliers and employees as received. Several examples of 20 capture solutions were prepared with the composition [C2mim] x [Cu] 1-x [SCN], where x is the molar fraction of ionic liquid and 1-x the molar fraction of copper salt (l) , by heating the ionic liquid to 373 KY by gradually adding different amounts of the copper salt (1) while stirring the solution. The results obtained are shown in Table 1. Table 1. Solubility of CuSCN in the ionic liquid {C2mim] [SCN]. Dissolution CuSCN weight Weight of [C2mim] [SCN] CuSCN concentration When cooling is captured (9) (9) (mol%) observed precipitates 1 2.51 41.06 7.84 No 2 3.63 29.95 14.45 No 3 5.33 29.25 20.24 No 4 6.79 27.88 25.31 No 5 10.50 34.51 29.75 No 6 11.29 31.46 33.30 Yes Example 2. Absorption capacity of pure CO This example shows the absorption capacities of CO at temperature of 293.15 K of 30 the capture solutions with the compositions indicated in Example 1, determined by the isocoric saturation method and considering non-ideal behavior of the gas phase. Figure 1 shows the pure CO absorption capacities of solutions 1-5 of Example 1 at the temperature of 293.15 K. The absorption capacities are expressedon a volumetric basis (mmol CO / L of solution) to take into account the differences between the densities of the different capture solutions. It can be clearly seen that as the concentration of the copper salt (l) increases, the CO absorption capacity of the capture solution is greater, as expected. This is due to the complexation reaction that takes place between the CO and the transition metal and that is characteristic of chemical absorption processes. Example 3. Effect of temperature on the absorption capacity of pure CO This example shows the influence of temperature on the process of chemical absorption of CO. Figure 2 gathers the absorption isotherms of pure CO in the solution of capture number 5 of Example 1 at different temperatures. In this case, it can be seen that the absorption capacity of pure CO increases significantly as the temperature decreases, since it is usual for this type of complexation reactions between transition metals and other ligands to have an exothermic behavior. Normally, chemical absorption processes have greater absorption capacity than physical solvents, but also higher energy requirements. In this case, the enthalpy of the complexation reaction between CO and copper (1) calculated for the capture solutions of Example 1 is -29.2 kJ / mol, which is significantly lower than that which can be found, for example, in C02 chemical absorption processes with amine solutions (up to -80 kJ / mol). This also implies that the energy needed to regenerate the CO capture solution will be less than that used in said conventional CO2 capture processes. Example 4. Regeneration of a capture solution and reuse capacity In this example, the reuse capacity of the capture solution 25 formed by the ionic liquid [C2mim] [SCN] and the CuSCN salt is shown. The desorption of the absorbed CO in each charge cycle is carried out by heating the capture solution to 333 K and decreasing the system pressure by means of a vacuum pump below 1 bar. In Figure 3, all the experiments performed in a single capture solution used in several cycles of loading and unloading CO are shown under different operating conditions. In Figure 3, it can be seen that regardless of the operating conditions and the number of loading and unloading cycles performed, the capture solution keeps the CO absorption capacity intact, so it is possible to completely regenerate it and restore its initial capacity of absorption of CO. 35 
    权利要求:
    Claims (15)
    [1]
    5 10 15 20 25 30 35 40 45 CLAIMS 1. Carbon monoxide (CO) capture solution comprising: a. an ionic liquid, made up of a cation and an anion, and b. a capture compound, characterized because the anion of the ionic liquid (a) is not an element belonging to the group of halogens (group 17) and because the capture compound (b) is a transition metal salt selected from among those that can form reversible complexes with CO.
    [2]
    2. Solution according to claim 1, wherein the ionic liquid has a viscosity of less than 0.1 Pa s.
    [3]
    3. Solution according to claim 1, wherein the cation of the ionic liquid is selected from the group of imidazoliums.
    [4]
    4. Solution according to claim 3, wherein the cation of the ionic liquid is selected from the group consisting of 1-ethyl-3-methylimidazolium, 1-butyl-3-methylimidazolium and 1-hexyl-3-methylimidazolium.
    [5]
    5. Solution according to claim 1, wherein the ionic liquid anion is selected from the group consisting of thiocyanate, acetate, trifluoroalkylsulfonate and trifluoroacetate.
    [6]
    6. Solution according to claim 5, wherein the anion of the ionic liquid is thiocyanate.
    [7]
    7. Solution, according to claim 1, wherein the transition metal salt is selected from the group consisting of copper (l) thiocyanate (CuSCN), copper (l) acetate (CuC02CH3), copper (l) trifluoromethanesulfonate (CUCF3S03) , copper (l) trifluoroacetate (CuCO2CF3).
    [8]
    8. Solution according to claim 7, wherein the transition metal salt is copper (I) thiocyanate.
    [9]
    9. Solution according to claim 1, formed by a solution of the metal salt of copper (l) thiocyanate (CuSCN) in the ionic liquid 1-ethyl-3-methylimidazolium thiocyanate.
    [10]
    10. A method for capturing and separating carbon monoxide gas (CO) from a gas stream, comprising the following steps: i. the contacting of the gaseous stream containing CO with a capture solution, as defined in claims 1-9, which removes the CO from said stream, ii. the selective and reversible reaction between CO and salt transition metal; andIii. Regeneration of the capture solution and recovery of the ca contained in it.
    [11]
    The method of claim 10, where step i) is carried out by increasing the pressure of the system until reaching a final pressure between 6 and 25 bar.
    [12]
    12. The method of claim 10, wherein step i) is carried out by cooling the capture solution to a temperature between 273 and 303 K.
    [13]
    13. The method of claim 10, wherein the gas stream contains ca along with other gases, primarily H2, ca2, CH4 and N2.
    [14]
    The method of claim 10, where step iii) is carried out by increasing the temperature of the capture solution until reaching a final temperature between 333 and 473 K, in one or more steps.
    [15]
    The method of claim 14, where step iii) is carried out by reducing the pressure of the system until reaching a final pressure between 0.1 and 1 bar, in one or more stages.
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    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    WO2009011577A1|2007-07-16|2009-01-22|Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno|Processes for separation of gases using ionic liquids|
    WO2015013076A1|2013-07-23|2015-01-29|Chevron Phillips Chemical Company Lp|Separations with ionic liquid solvents|
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